1,6-CH insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives

doi:10.1016/S0040-4039(01)01208-4

Tetrahedron Letters

Volume 42, Issue 35, 27 August 2001, Pages 6031-6033

https://doi.org/10.1016/S0040-4039(01)01208-4 Get rights and content

Abstract

Rare 1,6-CH insertion of naphthol- and anthrol-derived alkylidenecarbenes has been observed in modest yield. Reaction in deuterated solvent did not provide any evidence in support of a reaction mechanism that requires exchange of the migrating proton with solvent. The pyran-annelated aromatic products are formed only when opportunities for the more common 1,5-CH insertion process are blocked.

1,6-CH insertion of naphthol- and anthrol-derived alkylidenecarbenes has been observed in modest yield with substrates that have the more common 1,5-CH insertion option blocked.

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Acknowledgements

We thank the National Institutes of Health (GM37681) for financial support of this work.

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1,6-CH insertion of alkylidenecarbenes in 1-naphthol and 1-anthrol derivatives

Abstract

Section snippets

Acknowledgements

Tetrahedron

Tetrahedron

Angew. Chem., Int. Ed. Engl.